This invention relates to the oxidation of olefinic carbon-carbon double bonds to carbonyl groups. In another aspect, it relates to the use of a diluent system comprising at least two liquid phases with at least one being aqueous. In another aspect, it relates to the use of a two-phase diluent system with one being an aqueous phase and another being an organic phase. In another aspect, this invention relates to a process for the oxidation of olefinic carbon-carbon double bonds in which a multi-phase diluent system is used with at least one phase being aqueous and at least one other phase being an alcohol. In still another aspect, this invention relates to an olefin oxidation process in which a two-phase diluent system is employed with one phase being aqueous and the other phase being an alcohol. In yet another aspect, it relates to the use of a Pd/Cu/alkali metal or alkaline earth metal chloride catalyst in conjunction with a multi-phase diluent system for the oxidation of olefinic carbon-carbon double bonds to carbonyl groups. In yet another aspect, this invention relates to the addition of a suitable surfactant to such a reaction system.
The Wacker-type oxidation of ethylene to acetaldehyde using a palladium chloride/cupric chloride/hydrochloric acid catalyst in an aqueous solution has been modified and applied to the synthesis of methyl ketones from terminal olefins. However, major problems have been encountered in using the Wacker-type oxidation in the oxidation of higher olefins. One problem is that of reduced rates of reaction due to the low solubility of the olefin in the aqueous medium. Another major problem is the concomitant secondary oxidation of the ketone product which leads to poor selectivities and poor yield of desired product.